8/10/2010 @ 12:30PM

Cheap Times To Visit Pricey Places

If you want to visit such hot getaways as Hawaii, Aspen, New York City, Paris, or Napa, you can bring a large billfold. Or you can time your visit to the periods during the year when these places are at their most affordable.

When is the best time to visit to get the most bang for your buck? It varies from destination to destination. That can mean shoulder season or even off season, or finding that window in high season when rates take a dip, if only for a couple of weeks. And it’s worth the effort, because the savings can be anywhere from 20% to 50% off high-season prices. They may not be truly “cheap” at that point, but they often become affordable.

Take London, which provides sticker shock regardless of whether the pound has fallen. Both airfares and hotels fall between Oct. 15 and March 31, with the exception being the Christmas and New Year’s holiday period.

The caveats are weather and daylight. Wet, rainy and cold weather is not uncommon, and the lack of daylight is, um, profound. In midwinter the sun sets in London at 3:45 p.m. But if you accept that museums, the theater, and restaurants are where you’ll spend the lion’s share of your waking hours, you probably won’t mind it so much.

Then there’s Hawaii. How do you deal with a place where room rates seem uniformly high throughout the year? You go now, since the recession has left thousands of empty hotel rooms throughout the state. And to make sure the rate is even lower, plan on traveling between September and early December, which has long been the low season for travel to the Aloha State.

As for the Caribbean, the merry month of May represents the sweet spot for Caribbean travel. Prices have dropped as much as 50% from winter highs, the weather is still terrific, and the spring break crowds are gone. The weather gets warmer in June, but it can still be a terrific time to go. While July and August are quite hot, they might still be preferable to the weather in the U.S. at the same time. September through November represent the quietest time in the islands.

Of course, there is one caution in the Caribbean, and that’s hurricane season, which extends from June through November. You should have travel insurance and stay at a hotel that has a hurricane policy (with refunds clearly spelled out). It’s worth noting that hurricanes rarely, if ever, strike the southernmost islands in the Caribbean, such as Aruba, Barbados and Trinidad.

Then there’s New York City. While the recession has cut the average hotel rate in the Big Apple, you still need the deepest discount you can get. January through March represent the best time to get a deal in New York City. But dress warmly–those winds off the Hudson mean business.

Want to go skiing in a tony Western resort like Aspen without dipping into your kids’ college fund? Then go in early December. Other dates worth a look at are the entire month of January, excepting Martin Luther King Jr. weekend, and dates after March 20.

Balmy breezes and empty beaches are why Martha’s Vineyard and Nantucket are best during May and June. Before the private jet set arrive for a little R&R on these storied and pricey islands every summer and fall, most hotels offer weekend deals to entice mainlanders of all stripes. You’ll especially see a lot of midweek deals. You can stroll on these island beaches during May and June, but swimming is only for those with iron constitutions. These waters don’t really begin to warm up until July.

Of course, some places are not governed by season, like Moscow and Tokyo, and their high rates are pretty much stuck in the stratosphere. But if you pay close attention to the calendar, you’ll see that most places will give you a break.